Synthesis of New 3-[(Alkylthio)methyl]-1-hydroxy-2-phenylindoles

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 1069-1072 ◽  
Author(s):  
Sang Lee ◽  
Hyejin Kim ◽  
Yeon Park ◽  
Hyunsung Cho
Keyword(s):  
Reaction Pathways ◽  
Mechanistic Studies ◽  
One Pot

The syntheses of new 3-[(alkylthio)methyl]-1-hydroxy-2-phenylindoles are presented. The substrates, obtained by efficient three-step synthesis, were treated with various thiol nucleophiles in the presence of SnCl2·2H2O to provide target compounds, through the consecutive processes of reduction, condensation, and addition in one pot. The mechanistic studies on reaction pathways and the involved intermediates are described.

scholarly journals Pd/TOMPP-catalyzed telomerization of 1,3-butadiene: From biomass-based substrates to new mechanistic insights

2012 ◽  
Vol 84 (8) ◽  
pp. 1713-1727 ◽  
Author(s):  
Peter J. C. Hausoul ◽  
Pieter C. A. Bruijnincx ◽  
Bert M. Weckhuysen ◽  
Robert J. M. Klein Gebbink
Keyword(s):  
Catalyst Deactivation ◽  
Active Catalyst ◽  
Synthesis Method ◽  
Catalyst System ◽  
Reaction Pathways ◽  
Mechanistic Studies ◽  
One Pot ◽  
Highly Active ◽  
System A ◽  
Insight Into

Studies aimed at synthesizing surfactants from biomass-based feedstocks using Pd-catalyzed telomerization of 1,3-butadiene resulted in the development of a highly active catalyst system. A ligand screening was performed, and Pd/tris(2-methoxyphenyl)phosphine (TOMPP) was identified as the most promising catalyst. A solvent- and base-free protocol was developed, which allows efficient and selective conversion of a wide variety of polyol substrates (e.g., glycerol, diols, carbohydrates, and sugar alcohols). In the case of hemi-acetal bearing sugars, catalyst deactivation was observed and mechanistic studies showed that extensive formation of ligand-derived phosphonium species depleted the amount of available ligand. Stoichiometric coordination reactions gave insight into the phosphine alkylation mechanism and demonstrated the reversibility of the observed reaction. A simple and efficient one-pot synthesis method was developed for the preparation of [Pd((1-3,7,8η)-(E)-octa-2,7-dien-1-yl)(PR3)]+ complexes, which are key reactive intermediates. Based on these studies, an extended telomerization mechanism is proposed, which accounts for the formation of ligand-derived phosphonium species and the reversibility of reaction pathways.

scholarly journals PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

2021 ◽  
pp. 174751982098753
Author(s):  
Xiaofang Wu ◽  
Lei Zhou ◽  
Fangshao Li ◽  
Jing Xiao
Keyword(s):  
Acid Chloride ◽  
Bioactive Molecules ◽  
Mechanistic Studies ◽  
One Pot ◽  
Tert Butyl ◽  
Butyl Esters

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

scholarly journals Production of lactic acid from cellulose using solid catalyst

2019 ◽  
Vol 268 ◽  
pp. 07006 ◽  
Author(s):  
Sujitra Doungsri ◽  
P. Rattanaphanee ◽  
Aatichat Wongkoblap
Keyword(s):  
Lactic Acid ◽  
Batch Reactor ◽  
Nitrogen Pressure ◽  
Reaction Pathways ◽  
Solid Catalyst ◽  
One Pot ◽  
Solid Catalysts ◽  
Platform Chemicals ◽  
Acid And Base ◽  
The One

Lactic acid (LA), one of the important biomass derived platform chemicals, has been used in food and chemical industries, especially in biodegradable polymer as polylactic acid (PLA). The aim of this work is to study the one-pot production of LA from cellulose by using different solid catalysts. The reaction was conducted in a high pressure batch reactor and the catalyst used in this study were ZrO2 and Al2O3. The reaction was carried out at temperature of 200oC for 6 hr. and under nitrogen pressure of 1 MP. It was found that the production yield of LA were 8.02% and 6.63%, when the ZrO2 and Al2O3 catalysts were used respectively. The result indicated that the ZrO2 may effect on the LA production because of the acid and base sites of the ZrO2. Therefore, the reaction pathways for conversion of cellulose into lactic acid have been investigated, and developed the new conditions to achieve the higher yield.

Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: reactivity and mechanistic studies

2017 ◽  
Vol 53 (94) ◽  
pp. 12708-12711 ◽  
Author(s):  
Redouane Beniazza ◽  
Baptiste Abadie ◽  
Lionel Remisse ◽  
Damien Jardel ◽  
Dominique Lastécouères ◽  
...  
Keyword(s):  
Oxidizing Agent ◽  
Mechanistic Studies ◽  
One Pot ◽  
Metal Free ◽  
Low Intensity ◽  
Uva Irradiation

Cross dehydrogenative couplings on ethers are performed very effectively in a one-pot process using NFSI as oxidizing agent under low-intensity UVA irradiation in the presence of 2 mol% benzophenone.

scholarly journals One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

scholarly journals Modulation of Metal Species as Early Control Point for Ni-catalyzed Stereodivergent Semihydrogenation of Alkynes with Water

2021 ◽  
Author(s):  
Yuanqi Wu ◽  
Yuhui Ao ◽  
Chunhui Liu ◽  
Jinbo Zhao ◽  
Wenyu Gao ◽  
...  
Keyword(s):  
Control Point ◽  
Reaction Pathways ◽  
Metal Species ◽  
Mechanistic Studies ◽  
Triple Bonds ◽  
Valence States ◽  
High Yields ◽  
Nickel Species ◽  
Catalytic Cycles

Abstract A base-assisted metal species modulation mechanism enables Ni-catalyzed stereodivergent semihydrogenation of alkynes with water, delivering both olefinic isomers smoothly using cheap and nontoxic catalysts and additives. Different from most precedents, in which E-alkenes derive from the isomerization of Z-alkene products, the isomers were formed in orthogonal catalytic pathways. Mechanistic studies suggest base as a key early element in modulation of the reaction pathways: by adding different bases, nickel species with disparate valence states could be accessed to initiate two catalytic cycles toward different stereoisomers. The practicability of the method was showcased with nearly 70 examples, including internal and terminal triple bonds, enynes and diynes, affording semi-hydrogenated products in high yields and selectivity.

One-Pot Synthesis of Quinazolin-4(3H )-ones through Anodic Oxidation and the Related Mechanistic Studies

2018 ◽  
Vol 360 (24) ◽  
pp. 4764-4773 ◽  
Author(s):  
Liu Cao ◽  
Hengrui Huo ◽  
Haipeng Zeng ◽  
Yu Yu ◽  
Dengfu Lu ◽  
...  
Keyword(s):  
Anodic Oxidation ◽  
Mechanistic Studies ◽  
One Pot ◽  
One Pot Synthesis
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